Toluene → Methyl 2-((tert-butoxycarbonyl)amino)prop-2-enoate

HRID 1348947Notes

Reaction equation

HRID 1348947 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]([CH2:13]O)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(N(CC)CC)C.C1(C)C=CC=CC=1>O1CCCC1>[CH3:1][O:2][C:3](=[O:15])[C:4](=[CH2:13])[NH:5][C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7]

Participants

5

Reactant 3

HCID 1140TolueneHCID 8471TriethylamineHCID 495564Methyl N-(tert-butoxycarbonyl)serinate

Product 1

HCID 10932500Methyl 2-((tert-butoxycarbonyl)amino)prop-2-enoateYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-(tert-butyloxycarbonyl)-DL-serine methyl ester {5.48 g, Reference Example 15(a)} in tetrahydrofuran (60 mL) was treated with triethylamine (3.48 mL) followed by carbonyldiilmidazole (4.05 g). The mixture was stirred at room temperature overnight and then evaporated. The residue was extracted several times with tert-butyl methyl ether. The combined extracts were evaporated to give a colourless oil which was subjected to flash chromatography on silica eluting with toluene to give the title compound (3.64 g) as a colourless oil.

Workup

  1. customevaporated
  2. extractionThe residue was extracted several times with tert-butyl methyl ether
  3. customThe combined extracts were evaporated
  4. customto give a colourless oil which

Sources & evidence

ORD record
ord-7119e80321624dc89c5a25e02874c218
Source dataset
uspto-grants-2007_05
Patent number
US07211586B2

Reaction notes

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